((R)-3-Benzenesulfonyl-1,1,2-trimethyl-propoxy)-triethyl-silane | 135604-73-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ((R)-3-Benzenesulfonyl-1,1,2-trimethyl-propoxy)-triethyl-silane
• 英文别名: [(3R)-4-(benzenesulfonyl)-2,3-dimethylbutan-2-yl]oxy-triethylsilane
• CAS: 135604-73-8
• 化学式: C₁₈H₃₂O₃SSi
• 分子量: 356.602
• InChiKey: CVYZTKRAQWZTSS-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  23
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (5Z,7E)-(1S,3R)-1,3-bis<(t-butyldimethylsilyl)oxy>-9,10-secochola-5,7,10(19)-trien-24-al 、 ((R)-3-Benzenesulfonyl-1,1,2-trimethyl-propoxy)-triethyl-silane 在 正丁基锂 、 1,10-菲罗啉 、 二异丙胺 作用下， 生成 (3R,8R)-4-Benzenesulfonyl-8-{(1R,3aS,7aR)-4-[2-[(3S,5R)-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-2,3-dimethyl-2-triethylsilanyloxy-nonan-5-ol
  参考文献：
  名称：

  Synthesis of side-chain homologated analogs of 1,25-dihydroxycholecalciferol and 1,25-dihydroxyergocalciferol

  摘要：

  A novel synthesis of side-chain homologated analogs of vitamin D isomers has been described. The synthesis allows for the insertion of the double bond into the C-24 position of the side chain. The key synthetic step involves the coupling of a new C24-vitamin D synthon with the respective side-chain fragment. The method is illustrated by the preparation of (24E)-24,24a-dehydro-24,24-dihomo-1,25-dihydroxycholecalciferol (1) and (24b R)- and (24b S)-24,24-dihomo-1,25-dihydroxyergocalciferols (2 and 3). Trans geometry of the newly formed double bond in the side chain was confirmed by high field nuclear magnetic resonance spectra.

  DOI：

  10.1016/0039-128x(91)90052-w

文献信息

• 2-Methylene-19-nor-(20S-24S)-1alpha,25-dihydroxyvitamin D2
  申请人：DeLuca F. Hector

  公开号：US20060183716A1

  公开（公告）日：2006-08-17

  Compounds of formula I are provided where X 1 , X 2 , and X 3 are independently selected from H or hydroxy protecting groups. Such compounds may be used in preparing pharmaceutical compositions and are useful in treating a variety of biological conditions.

  提供了化学式I的化合物，其中X1、X2和X3分别独立地选择自H或羟基保护基团。这些化合物可用于制备药物组合物，并且在治疗各种生物状况方面非常有用。
• Synthesis, CYP24A1-Dependent Metabolism and Antiproliferative Potential against Colorectal Cancer Cells of 1,25-Dihydroxyvitamin D2 Derivatives Modified at the Side Chain and the A-Ring
  作者：Magdalena Milczarek、Michał Chodyński、Anita Pietraszek、Martyna Stachowicz-Suhs、Kaori Yasuda、Toshiyuki Sakaki、Joanna Wietrzyk、Andrzej Kutner

  DOI：10.3390/ijms21020642

  日期：——

  another in their absolute configuration at C-24, namely (24S)- and (24R)-1,25-dihydroxy-19-nor-20a-homo-ergocalciferols (PRI-5105 and PRI-5106, respectively), and evaluated their activity. Unexpectedly, despite introducing double-point modifications, both analogs served as very good substrates for the vitamin D-hydroxylating enzyme. Irrespective of their absolute C-24 configuration, PRI-5105 and PRI-5106

  实验数据表明，低钙的维生素D衍生物（VDDs）在体外和体内均表现出抗癌特性。在寻找维生素D类似物作为潜在抗癌剂的过程中，我们研究了1,25-二羟基麦角钙化醇（1,25D2）衍生物侧链中的手性对其活性的影响。在这项研究中，我们在侧链和A环上合成了修饰的类似物，它们在C-24处的绝对构型彼此不同，即（24S）-和（24R）-1,25-二羟基-19- nor-20a-homo-ergocalciferols（分别为PRI-5105和PRI-5106），并评估了它们的活性。出乎意料的是，尽管引入了双点修饰，但两种类似物还是维生素D-羟化酶的非常好的底物。不管它们的绝对C-24配置如何，PRI-5105和PRI-5106对CYP24A1依赖性代谢失活显示出相对较低的耐药性。此外，两个VDD均显示出对HT-29大肠癌细胞具有相似的抗增殖活性，高于维生素D的主要生物活性代谢物1,25D3。此外，PRI-